Amanda Lepore

Who: America's favorite post-op transsexual, Lepore is a ubiquitous figure on the downtown NYC nightlife scene and a muse to superstar photographer David LaChapelle.

Backstory: Born Armand Lepore in Cedar Hill, NJ, Lepore says she started wearing women's clothes at age 14. "Ever since I can first remember, I knew I was a girl. I couldn't understand why my parents were dressing me up in boys clothing. I thought they were insane." As a teenager, she befriended a transsexual at a club who started giving her hormone pills in exchange for Lepore's elaborate, handmade outfits; by the time she reached her senior year of high school, she'd undergone sexual reassignment surgery, paid for by her high school boyfriend's parents. Lepore soon moved in with her boyfriend and his sympathetic family, and for five years she remained there, under virtual house arrest, as her boyfriend didn't want her to be seen in public, lest she out him. Lepore finally escaped to New York, and worked as a dominatrix to pay the bills before falling in with the nightlife scene via Michael Alig's infamous "Disco 2000" parties.

Of note: For much of the 1990s, Lepore was a fixture at downtown Manhattan clubs where she was paid, as she puts it, "to dress up, look freaky and flashy and over the top, and to dance." But she also earned pop culture fame thanks to her close friendship with photographer David LaChapelle, who made her his muse. Over the years, she's been featured in countless LaChapelle photographs, and even graced a LaChapelle-designed Swatch watch. (The "Time Tranny" featured a close-up shot of Lepore and has since become a collector's item.) Lepore remains a fixture at events (where she can often be found alongside similarly colorful nightlife staples like Richie Rich and Lady Bunny), but she's also pursuing a music career. She released her debut album, featuring the singles "Champagne" and "My Hair Looks Fierce," in 2007.

The look: Lepore's over-the-top look includes sky-high heels, massively swollen lips and drawn-on eyebrows. Proving that you really do have to suffer for beauty, Lepore's undergone a nose job, cosmetic rib surgery, permanent lip implants, three breast enlargements, butt implants and "eye-slanting," to make her look more feline. And then, of course, there's the sexual reassignment surgery: Ms. Lepore proudly possesses an artificially-constructed vagina.

Personal: Lepore lives near Gramercy Park and is single. She says one serious relationship ended recently because her beau apparently wasn't a fan of her "party outfits." Go figure.

Soundbite: LaChapelle explained, "When I told her that silicone is dangerous, she said, 'I don't care, as long as I look beautiful in the coffin.'"